Synthesis and biological evaluation of 6-nitro-1,2,4-triazoloazines containing polyphenol fragments possessing antioxidant and antiviral activity.

Autor: Ulomskiy EN; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Organic and Biomolecular Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation; Institute of Organic Synthesis, Ural Division of RAS, 620990, 22/20 S. Kovalevskoy st./Akademicheskaya st., Yekaterinburg, Russian Federation., Ivanova AV; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Analytical Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Gorbunov EB; Institute of Organic Synthesis, Ural Division of RAS, 620990, 22/20 S. Kovalevskoy st./Akademicheskaya st., Yekaterinburg, Russian Federation., Esaulkova IL; Pasteur Institute for Epidemiology and Microbiology, 197101, 14 Mira st., Saint Petersburg, Russian Federation., Slita AV; Pasteur Institute for Epidemiology and Microbiology, 197101, 14 Mira st., Saint Petersburg, Russian Federation., Sinegubova EO; Pasteur Institute for Epidemiology and Microbiology, 197101, 14 Mira st., Saint Petersburg, Russian Federation., Voinkov EK; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Organic and Biomolecular Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Drokin RA; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Organic and Biomolecular Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Butorin II; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Organic and Biomolecular Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Gazizullina ER; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Analytical Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Gerasimova EL; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Analytical Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation., Zarubaev VV; Pasteur Institute for Epidemiology and Microbiology, 197101, 14 Mira st., Saint Petersburg, Russian Federation. Electronic address: zarubaev@gmail.com., Rusinov VL; Ural Federal University Named After the First President of Russia B. N. Yeltsin, Department of Organic and Biomolecular Chemistry, 620002, 19 Mira St., Yekaterinburg, Russian Federation; Institute of Organic Synthesis, Ural Division of RAS, 620990, 22/20 S. Kovalevskoy st./Akademicheskaya st., Yekaterinburg, Russian Federation.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry letters [Bioorg Med Chem Lett] 2020 Jul 01; Vol. 30 (13), pp. 127216. Date of Electronic Publication: 2020 Apr 27.
DOI: 10.1016/j.bmcl.2020.127216
Abstrakt: Stable σ-adducts of azolo[5,1-c]triazines and azolo[1,5-a]pyrimidines with different polyphenols were synthesized and their antioxidant and antiviral activity were investigated. Their affinity to viral hemagglutinin was assessed using molecular modelling. The phloroglucinol-modified azolo-azines possessed the highest virus-inhibiting activity. According to the results of the study of antioxidant properties of compounds, the most promising ones exhibiting highest antioxidant capacity were adducts containing in their structure pyrogallol and catechol residues and 6-nitro-triazolotriazin-7-ol scaffold. No correlation between antioxidant and virus-inhibiting activity of compounds studied was detected. The most active compounds demonstrated the ability to prevent binding of viral hemagglutinin with cellular receptor as shown in hemagglutination inhibition assay. Our results demonstrate that polyphenol-modified azolo-azines are prospective for further optimization as potential antivirals and that their action is directed against viral hemagglutinin.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2020 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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